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Title: Studies on the chemical modification of peptides related to the enkephalins
Author: Treadgold, R. C.
Awarding Body: University College of Swansea
Current Institution: Swansea University
Date of Award: 1981
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This thesis has been concerned with an investigation into the chemical modification of peptides related to the enkephalins by the preparation of organosilicon derivatives and by acylation. Studies on the chemical modification of biologically active peptides have been reviewed together with the isolation and characterisation of the enkephalin peptides. Recent investigations on the N-acylation of amino acid and peptide derivatives have also been surveyed. Several derivatives of enkephalin related peptides have been synthesised by various coupling methods and using different protecting groups. Techniques have been developed for the use of organosilicon reagents in the synthesis of hydantoin derivatives of polypeptides from N-benzyloxycarbonyl protected peptides containing a glycine residue at the 2 position. The biological analysis of a deprotected hydantoin derivative of leucine-enkephalin has been described. This displayed a depressant effect on the central nervous system. A method has been described for the incorporation of an N-acyl residue at the Gly2-Gly3 bond in leucine-enkephalin. Proof of the structure of N-acylated derivatives was performed by both spectroscopic methods and chemical fragmentation. Subsequent biological analysis of a suitably deprotected N-acylated enkephalin derivative incorporating a fatty acid residue has been performed. The result supported previously reported observations that the presence of the Gly3 N-H group is essential for in vitro activity. No conclusive evidence was obtained for antagonist activity being exhibited by this product.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available